Olivia: The Woman Who Falls for the Wrong Person Twice

When the play begins, Olivia is in mourning for her dead brother and has sworn off men for seven years. She abandons this vow the moment Cesario speaks to her. Her falling for Viola-in-disguise is not presented as foolishness. It is presented as the most alive she has been since her brother died. The comedy is that she has chosen someone who cannot return her love and cannot explain why.

She is direct in a way that most of Shakespeare's women are not allowed to be. She tells Cesario she loves him. She sends him a ring as a token after one conversation. She proposes to Sebastian, having met him for about ten minutes, thinking he is Cesario. She wants what she wants and she acts.

The resolution she gets (married to Sebastian, a man she has never had a real conversation with) is technically a happy ending. The play does not ask us to look too closely at it. Sebastian seems pleased. Olivia is satisfied. That has to be enough.